Benzaldehyde, 5-chloro-2-hydroxy-, oxime → 5-Chloro-2-hydroxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 5-chloro-2-hydroxybenzaldoxime (4.2 g) in acetic anhydride (15 ml) was heated for 4 hours at reflux, then allowed to stand for 16 hours at ambient temperature. The mixture was added to a vigorously stirred ice-water mixture and after one hour the resulting solid was collected by filtration. 2M Sodium hydroxide solution (120 ml) was added to a stirred solution of this solid in methanol (50 ml) and the mixture stirred for 20 minutes. The pH of the mixture was then adjusted to 4.0 with 2M hydrochloric acid solution. The mixture was cooled to 4° C. and the white precipitate collected by filtration to give 4-chloro-2-cyanophenol (2.6 g), m.p. 166°-168° C.; NMR (CDCl3 /d6 -DMSO): 6.69(1H,d,J=8 Hz), 7.04(1H,dd,J=8,2.5 Hz), 7.11(1H,d,J=2.5 Hz), 10.33(1H,s).

Provenance & Evidence